HCID 71295625, compound → HCID 136341365, compound

HRID 1776814Notes

Reaction equation

HRID 1776814 reaction equation
C([O:8][C:9]1[CH:10]=[CH:11][C:12]([C:25]2[C:26]([N:45]([CH3:50])[S:46]([CH3:49])(=[O:48])=[O:47])=[CH:27][C:28]3[O:32][C:31]([C:33]4[CH:38]=[CH:37][C:36]([F:39])=[CH:35][CH:34]=4)=[C:30]([C:40]([NH:42][CH3:43])=[O:41])[C:29]=3[CH:44]=2)=[N:13][C:14]=1[C:15]1[NH:24][C:18]2=[CH:19][N:20]=[CH:21][C:22]([F:23])=[C:17]2[CH:16]=1)C1C=CC=CC=1>C1COCC1.[Pd]>[F:23][C:22]1[CH:21]=[N:20][CH:19]=[C:18]2[NH:24][C:15]([C:14]3[N:13]=[C:12]([C:25]4[C:26]([N:45]([CH3:50])[S:46]([CH3:49])(=[O:47])=[O:48])=[CH:27][C:28]5[O:32][C:31]([C:33]6[CH:38]=[CH:37][C:36]([F:39])=[CH:35][CH:34]=6)=[C:30]([C:40]([NH:42][CH3:43])=[O:41])[C:29]=5[CH:44]=4)[CH:11]=[CH:10][C:9]=3[OH:8])=[CH:16][C:17]=12

Participants

4

Reactant 1

HCID 71295625HCID 71295625, compound

Product 1

HCID 136341365HCID 136341365, compoundYield 92%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a degassed solution of 5-(5-(benzyloxy)-6-(4-fluoro-1H-pyrrolo[2,3-c]pyridin-2-yl)pyridin-2-yl)-2-(4-fluorophenyl)-N-methyl-6-(N-methylmethylsulfonamido)benzofuran-3-carboxamide (150 mg, 0.22 mmol) was dissolved in THF (5 mL) and charged with 10% palladium on carbon (0.1 g). The mixture was hydrogenated at room temperature under hydrogen pressure for 4 hours. The reaction mixture was filtered and the filtrate was extract with EtOAc and washed with H2O, brine, dried over Na2SO4. After concentrated, the resulting residue was purified using prep-TLC to provide 5-(6-(4-fluoro-1H-pyrrolo[2,3-c]pyridin-2-yl)-5-hydroxypyridin-2-yl)-2-(4-fluorophenyl)-N-methyl-6-(N-methylmethylsulfonamido)benzofuran-3-carboxamide (120 mg, yield: 92%). 1H-NMR (CDCl3, 400 MHz) δ 12.00 (s, 1H), 11.17 (s, 1H), 8.67 (s, 1H), 8.52 (s, 1H), 8.01 (t, J=6.0 Hz, 3H), 7.91 (s, 1H), 7.52 (s, 2H), 7.41˜7.35 (m, 3H), 3.19 (s, 3H), 2.95 (s, 3H), 2.80 (d, J=4.0 Hz, 3H). MS (M+H)+: 604.

Workup

  1. customwas hydrogenated at room temperature under hydrogen
  2. customfor 4 hours
  3. filtrationThe reaction mixture was filtered
  4. extractionthe filtrate was extract with EtOAc
  5. washwashed with H2O, brine
  6. dry with materialdried over Na2SO4
  7. concentrationAfter concentrated
  8. customthe resulting residue was purified

Sources & evidence

ORD record
ord-5288bd32f16548488998b036960b132c
Source dataset
uspto-grants-2016_02
Patent number
US09265773B2

Reaction notes

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